Interfacial Generation of a Carbanion: The Key Step of PTC Reaction Directly Observed by Second Harmonic Generation

Interfacial Generation of a Carbanion: The Key Step of PTC Reaction Directly Observed by Second... We present the first unambiguous evidence of the interfacial mechanism of phase‐transfer catalysis (PTC) by direct observation of the formation of carbanions in the interfacial region between the aqueous and the organic phase by using a surface‐sensitive spectroscopic method known as second harmonic generation (SHG). Ion exchange of carbanions adsorbed at the surface after addition of lipophilic tetraalkylammonium salts (TAA) to organic phase and transport of the lipophilic ion‐pairs to the organic phase is observed. Results allow for the formulation of a more detailed mechanism of PTC. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Interfacial Generation of a Carbanion: The Key Step of PTC Reaction Directly Observed by Second Harmonic Generation

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201705597
Publisher site
See Article on Publisher Site

Abstract

We present the first unambiguous evidence of the interfacial mechanism of phase‐transfer catalysis (PTC) by direct observation of the formation of carbanions in the interfacial region between the aqueous and the organic phase by using a surface‐sensitive spectroscopic method known as second harmonic generation (SHG). Ion exchange of carbanions adsorbed at the surface after addition of lipophilic tetraalkylammonium salts (TAA) to organic phase and transport of the lipophilic ion‐pairs to the organic phase is observed. Results allow for the formulation of a more detailed mechanism of PTC.

Journal

Chemistry - A European JournalWiley

Published: Jan 15, 2018

Keywords: ; ; ; ;

References

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